Best apartment offers in Chicago, IL

10028 available apartment offers

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Chicago, IL apartments
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10028 Holiday apartments in Chicago, IL

Best family friendly Chicago, IL Holiday Apartments and Self Contained Accommodations

Among the 10028 accommodations in Chicago, IL, here are the 4 best family friendly holiday apartments

Super Deluxe Avondale Studio Near Transit - Chicago, IL
9.7 6 reviews
Chicago, IL
11/10 – 17/10
NZ$316/nighttotal: NZ$1896 (6 )

Super Deluxe Avondale Studio Near Transit

1 1
apartment , Chicago
This deluxe studio apartment in Chicago's Avondale district is a mere 800 metres to 1 kilometre walk from Ravenswood, Lincoln Square, and Edgewater, with the Damen brown line a 10-minute walk away for direct access to the city centre.
This family-friendly accommodation offers private living for up to four guests, featuring two beds, a full kitchen with essential appliances, air conditioning, and complimentary internet, making it ideal for both short and extended stays.
Heart Of Lincoln Park - Chicago, IL
9.4 8 reviews
Chicago, IL
24/06 – 26/06
NZ$743/nighttotal: NZ$1486 (2 )

Heart Of Lincoln Park

2 2
apartment , Chicago
This Lincoln Park flat offers a prime Chicago location, within easy walking distance of Lincoln Park itself, North Avenue Beach, and renowned eateries such as Lou Malnati's Pizzeria and Small Cheval.
The two-bedroom, one-bathroom apartment sleeps five, includes in-unit laundry facilities, fast Wi-Fi, and a fully equipped kitchen with a fridge, microwave, and dishwasher; nearby attractions include Lincoln Park Zoo, Wrigley Field, and the United Center.
Pilsen Art Center Family Friendly 3br Retreat With Free Parking Near Medical District, Douglas Park And University Illinois Chicago - Chicago, IL
10 1 review
Chicago, IL
11/07 – 14/07
NZ$672/nighttotal: NZ$2016 (3 )

Pilsen Art Center Family Friendly 3br Retreat With Free Parking Near Medical District, Douglas Park And University Illinois Chicago

3 2
apartment , Chicago
This three-bedroom apartment in Chicago's Pilsen neighbourhood is situated approximately 3.2 kilometres from the United Centre and 7.2 kilometres from Union Station, Grant Park, and the CIBC Theatre.
The 139-square-metre property features two bathrooms, a fully equipped kitchen, private parking, a terrace, garden, and accommodates up to 15 guests, offering free Wi-Fi and convenient access to public transport.
Chicago 3br Oasis Near Downtown & United Center - Chicago, IL
Chicago, IL
28/06 – 01/07
NZ$504/nighttotal: NZ$1512 (3 )

Chicago 3br Oasis Near Downtown & United Center

3 2
apartment , Chicago
This Chicago three-bedroom flat is located 2.25 kilometres from the United Center and offers convenient access to downtown attractions such as Union Station and the Willis Tower, both 5.15 kilometres away.
This family-friendly residence spans 1000 square metres, features three bedrooms, two bathrooms, and accommodates up to 14 guests with amenities including air conditioning, a fully equipped kitchen with a dishwasher, and free WiFi, plus a balcony and private parking.

Best Chicago, IL holiday apartments with a balcony

Spacious Downtown Penthouse | Vintage, Balcony&gym - Chicago, IL
9.6 16 reviews
Chicago, IL
29/07 – 03/08
NZ$2053/nighttotal: NZ$10265 (5 )

Spacious Downtown Penthouse | Vintage, Balcony&gym

1 1
apartment , Chicago
This downtown Chicago penthouse offers a prime location near the Willis Tower and Cloud Gate, providing easy access to State Street and Michigan Avenue.
The 116 square metre (1248 square foot) flat features one bedroom, two bathrooms, sleeps seven guests, and includes a fully equipped kitchen, in-unit laundry, a balcony with city views, and access to a building gym.
The Penthouse, Lux Stay Near Downtown, Uofc & Lake - Chicago, IL
9.2 38 reviews
Chicago, IL
29/06 – 02/07
NZ$539/nighttotal: NZ$1617 (3 )

The Penthouse, Lux Stay Near Downtown, Uofc & Lake

2 2
apartment , Chicago
This Chicago penthouse apartment, near the University of Chicago campus and approximately 8km from Downtown Chicago, offers easy access to Lake Michigan and Oakwood Beach (a 17-minute walk away).
The 135-square-metre (1453 sq ft) property boasts two bedrooms, two bathrooms, a fully equipped kitchen, and a terrace, accommodating up to seven guests and providing free Wi-Fi and toiletries.
Modern 3br Apartment Near North Ave Shops - Chicago, IL
Chicago, IL
01/07 – 31/07
NZ$817/nighttotal: NZ$24510 (30 )

Modern 3br Apartment Near North Ave Shops

3 1
apartment , Chicago
This spacious three-bedroom flat is situated in Chicago's Old Town/Lincoln Park/Clybourn Corridor area, placing you a short walk from the Second City Theatre and a few kilometres from Lincoln Park Zoo and the lakefront via the North Branch Trail.
This 90-square-metre residence accommodates up to eight guests with three bedrooms, two bathrooms, a fully equipped kitchen featuring stainless steel appliances, and in-unit laundry facilities, all offering city views and individually controlled air conditioning.
Blueground | River North, Pool & W/d, Nr Mile - Chicago, IL
Chicago, IL
01/08 – 30/06
NZ$241/nighttotal: NZ$80253 (333 )

Blueground | River North, Pool & W/d, Nr Mile

1 1
apartment , Chicago
This stylish Chicago apartment, offered by Blueground, is situated in the River North neighbourhood, a 0.8 km walk from Michigan Avenue's shopping and the Merchandise Mart, and a similar distance from the Loop.
The 77 square metre flat features one bedroom, one bathroom, sleeps two guests, and includes a fully-equipped kitchen, in-unit laundry, balcony, and access to a building swimming pool and sauna.

Frequently asked questions about apartment rentals in Chicago, IL

  • What are the must-see attractions for a 2 days stay in Chicago, IL?

    For a two-day trip, you can't miss the iconic Willis Tower (formerly Sears Tower) for panoramic views of the city. Then, explore Millennium Park, home to Cloud Gate, nicknamed 'The Bean', and the Crown Fountain with its interactive water displays. Finally, stroll along Navy Pier for its Ferris wheel, shops, and restaurants.
  • What are the best apartments in Chicago, IL?

  • Which neighborhoods in Chicago, IL are best for renting an apartment?

    For a vibrant, walkable neighbourhood, consider Lincoln Park with its green spaces and Lake Michigan access. If you prefer a more historic feel, try the Gold Coast, known for its elegant architecture. For a more affordable option with great restaurants and nightlife, check out Wicker Park.
  • What are the best apartments with a pool in Chicago, IL?

  • What are the top cultural and historical sites in Chicago, IL?

    Chicago is brimming with cultural and historical gems. The Art Institute of Chicago houses masterpieces by Monet and Van Gogh, while the Field Museum boasts dinosaur skeletons and ancient Egyptian artefacts. For a taste of history, visit the Chicago Cultural Center, a stunning building with free concerts and exhibitions, or the Museum of Science and Industry.
  • What are the best apartments with a jacuzzi in Chicago, IL?

  • What makes Chicago, IL unique or famous?

    Chicago is known for its stunning architecture, from the towering skyscrapers of the Loop to the charming brownstones of the Gold Coast. It's also a culinary powerhouse, with world-class restaurants and a renowned deep-dish pizza scene. And don't forget the vibrant arts and culture scene, with world-class museums, theatres, and music venues.
  • What are the best apartments for families and kids in Chicago, IL?

  • Where can you find the best local markets and street food in Chicago, IL?

    For a taste of Chicago's diverse food scene, head to Maxwell Street Market on Sundays for a mix of local produce, crafts, and street food. The Wicker Park Farmers Market on Saturdays offers fresh, seasonal produce, while the Green City Market in Lincoln Park has a wide selection of local vendors.
  • What are the best pet friendly apartments in Chicago, IL?

  • How is the public transportation system in Chicago, IL?

    Chicago has a reliable and extensive public transportation system, the 'L', which is a combination of elevated trains and underground subway lines. It's a great way to get around the city, especially during rush hour. You can also use the CTA buses for more local travel.
  • What are the best apartments with parking in Chicago, IL?

  • Which seasonal events or festivals should apartment renters look forward to in Chicago, IL?

    Chicago is a city that comes alive with seasonal events. In the spring, enjoy the Chicago Blues Festival, while summer brings the Taste of Chicago food festival. Autumn is perfect for the Chicago Marathon, and winter offers festive holiday markets and ice skating at Millennium Park.
  • What amenities are typically included in apartments in Chicago, IL?

    Apartments in Chicago typically include central heating and air conditioning, in-building laundry facilities, and sometimes a gym or a rooftop terrace. Some newer buildings may also offer amenities like a swimming pool, a dog park, or a resident lounge.
  • What leisure activities are available for relaxation in Chicago, IL?

    For relaxation, Chicago offers a variety of options. You can stroll along the Lakefront Trail for stunning views of Lake Michigan, visit the Lincoln Park Zoo for a free day out, or take a boat tour on the Chicago River. For a quieter experience, explore the Garfield Park Conservatory, a beautiful greenhouse with exotic plants.

Destinations nearby

Best Chicago, IL holiday apartments with parking

Luxury Loft Collection 01 - Terrace - River North - Chicago, IL
9.8 18 reviews
Chicago, IL
18/06 – 20/06
NZ$2823/nighttotal: NZ$5646 (2 )

Luxury Loft Collection 01 - Terrace - River North

3 2
apartment , Chicago
This luxurious River North loft, in a new building, offers private elevator access and is conveniently located near the Chicago Theatre and Art Institute.
The 220 square metre (232 square meters converted to square metres) property boasts three bedrooms, three bathrooms, sleeps fourteen, and includes a chef's kitchen with Gaggenau appliances, a terrace with cityscape views, and secure parking.
Luxury Loft Collection Combo 902/903 Terrace - Chicago, IL
9.8 13 reviews
Chicago, IL
13/07 – 15/07
NZ$2201/nighttotal: NZ$4402 (2 )

Luxury Loft Collection Combo 902/903 Terrace

6 8
apartment , Chicago
This luxurious River North dwelling is ideally situated in Chicago's city centre, within easy walking distance of many restaurants and Chicago's main nightlife.
Offering over 5,000 square feet of space across two side-by-side lofts, this six-bedroom, six-bathroom property sleeps 16+ guests and boasts private elevator access, a terrace, secure parking, and chef's kitchens in each loft.
Private Lincoln Park Condo With 2 Parking Spots - Chicago, IL
9.9 131 reviews
Chicago, IL
27/06 – 05/07
NZ$854/nighttotal: NZ$6832 (8 )

Private Lincoln Park Condo With 2 Parking Spots

1 4
apartment , Chicago
This Lincoln Park flat, in a historically significant 1895 building, offers convenient access to Lincoln Park's attractions, within easy walking distance of many landmarks.
The two-bedroom, one-bathroom apartment sleeps six, boasting a fully-remodelled kitchen, a private balcony, two off-street parking spaces, a 75" 4K Smart TV, and high-speed fibre internet; a friendly black lab, Buck, may even greet you.
Modern House | 5 Beds | 3 Parking | Near Dt & Lake - Chicago, IL
9.9 35 reviews
Chicago, IL
28/06 – 02/07
NZ$850/nighttotal: NZ$3400 (4 )

Modern House | 5 Beds | 3 Parking | Near Dt & Lake

1 7
apartment , Chicago
This West Ridge apartment, situated approximately 8-10 km from the Magnificent Mile and Navy Pier, offers easy access to public transport connecting to the Red Line and downtown Chicago.
The four-bedroom, two-bathroom dwelling comfortably accommodates up to 12 guests, boasting a fully equipped kitchen, fenced backyard with grill, and parking for three cars, plus additional street parking; nearby amenities include Walgreens, Potbelly, and Chipotle.

Neighborhoods and points of interest in Chicago, IL

Best Chicago, IL holiday apartments with air conditioning

Nina's Cozy Room - Chicago, IL
Chicago, IL
18/06 – 31/08
NZ$108/nighttotal: NZ$7992 (74 )

Nina's Cozy Room

1 2
apartment , Chicago
This studio flat is located in Chicago's Belmont Cragin district, offering convenient transit access to the city centre and proximity to the Brickyard Mall, local bakeries, and eateries.
This sunlit studio accommodates two guests and features air conditioning, internet, and a modern bathroom, making it suitable for solo travellers or couples exploring Chicago.
Condo In Chicago Bronzeville 9 Mins To Downtown #3 - Chicago, IL
9.8 29 reviews
Chicago, IL
22/06 – 26/06
NZ$437/nighttotal: NZ$1748 (4 )

Condo In Chicago Bronzeville 9 Mins To Downtown #3

1 4
apartment , Chicago
This Bronzeville penthouse apartment, a two-minute walk from the Green Line and 1.6km from downtown Chicago, offers easy access to 31st Street Beach (1.6km) and the Museum Campus (2.4km).
Sleeping up to seven guests, this three-bedroom, two-bathroom dwelling boasts a fully equipped kitchen, free street parking, and self check-in; amenities include fast Wi-Fi, and central heating and cooling.
Enjoy In-unit Laundry A King Bed! - Chicago, IL
9.7 141 reviews
Chicago, IL
09/10 – 13/10
NZ$555/nighttotal: NZ$2220 (4 )

Enjoy In-unit Laundry A King Bed!

1 2
apartment , Chicago
This West Ridge basement flat is a 0.8-kilometre walk from Devon Avenue, offering easy access to diverse restaurants and shops, and is a short drive from Lake Michigan beaches.
The self-contained apartment sleeps four, features a private garden, in-unit laundry, parking, and a fully equipped kitchen including a dishwasher, and is conveniently located near Jewel-Osco, Target and Walmart supermarkets.
Charming|comfortable|1br|lincoln Square - Chicago, IL
9.6 193 reviews
Chicago, IL
30/06 – 31/07
NZ$361/nighttotal: NZ$11191 (31 )

Charming|comfortable|1br|lincoln Square

1 1
apartment , Chicago
This one-bedroom flat is situated in Lincoln Square, a lively neighbourhood just a short walk from restaurants, breweries, the Davis Theater and unique shops. The apartment has received excellent ratings for its location, cleanliness and overall experience.
The flat is located on the first floor and comfortably sleeps two guests. It comes with a fully equipped kitchen, a smart TV with Netflix, free on-street parking and air conditioning.
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